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Photoresist compositions

a composition and composition technology, applied in the field of photoresist compositions, can solve the problems of line collapse, affecting the performance of films, and becoming more important to solv

Inactive Publication Date: 2004-04-15
FUJIFILM ELECTRONICS MATERIALS US
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Benefits of technology

This patent is about a photosensitive composition that can be used in the manufacture of semiconductor devices. The composition has high resolution, excellent photospeed, and depth of focus. It also has decreased line collapse and film thickness dependence. The composition includes a first photoacid generator compound, a second photoacid generator compound, a polymer component, and a solvent. The first photoacid generator compound has the structure A, and the second photoacid generator compound has the structure B. The polymer component has an alkali solubility that is suppressed by acid sensitive moieties and returned by treatment with an acid and optionally heat. The composition can also contain additives such as nitrogenous bases, dissolution inhibitors, coating additives, dyes, and surfactants.

Problems solved by technology

As the required resolution becomes smaller, previously minor problems become more important to solve.
Two such problems are a dependence of performance on film thickness and line collapse.

Method used

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  • Photoresist compositions
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Examples

Experimental program
Comparison scheme
Effect test

synthesis example 1

PAG Synthesis Example 1

[0071] Synthesis of 4-(1-butoxyphenyl)diphenylsulfonium mesylate

[0072] In a 500 ml, round bottom flask equipped with a reflux condenser was combined n-butyl phenyl ether (40.4 g, 0.269 mol), diphenylsulfoxide (48 g, 0.237 mol) and Eaton's Reagent (154 g). An exothermic reaction occurred. The reaction mixture was maintained at 50-55.degree. C. with stirring for 5 hours. The reaction mixture was then added to deionized water (1200 ml). This mixture was stirred for 30 minutes. The mixture was extracted two times with toluene (2.times.300 ml). The pH of the lower aqueous layer was adjusted to 8-8.5 by addition of a 25% aqueous solution of tetramethylammonium hydroxide (573.0 g).

synthesis example 2

PAG Synthesis Example 2

[0073] Synthesis of 2,4,6-trimethylphenyidiphenylsulfonium mesylate

[0074] In a 1 L, round bottom flask equipped with a reflux condenser was combined 1,3,5-trimethylbenzene (40 g, 0.333 mol), diphenylsulfoxide (67.3 g, 0.333 mol) and Eaton's Reagent (160 g). An exothermic reaction occurred. The reaction mixture was maintained at 50-55.degree. C. with stirring for 5 hours. The reaction mixture was then added to deionized water (800 ml). This mixture was stirred for 30 minutes. The mixture was extracted two times with toluene (2.times.250 ml). The pH of the lower aqueous layer was adjusted to 8-8.5 by addition of a 25% aqueous solution of tetramethylammonium hydroxide (889.6 g).

synthesis example 3

PAG Synthesis Example 3

[0075] Synthesis of sodium bis-(perfluorobutanesulfonyl)imide

[0076] In a 250 ml beaker equipped with a stirbar and a pH meter was combined bis-(perfluorobutanesulfonyl) amide (15 g, 60% acid w / w in water, 0.0155 mol) and deionized water (105 g). To the solution, sodium hydroxide (approximately 1.9 g, 33% w / w in water) was slowly added until the pH was above 7.0. The solution became viscous. The solution was maintained at room temperature with stirring for 15 minutes. The salt solution was used immediately and without further work-up in subsequent PAG synthesis.

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Abstract

Radiation sensitive compositions for use in producing a patterned image on a substrate comprise: e) a first photoacid generator (PAG) compound P1, which comprises one or more compounds of the structure (A); f) a second photoacid generator compound P2 which comprises one or more compounds of the structure (B); and g) a polymer component comprising an alkali soluble resin component whose alkali solubility is suppressed by the presence of acid sensitive moieties and whose alkali solubility is returned by treatment with an acid and, optionally, heat; wherein said polymer comprises one or more polymers comprising the monomer unit (C); and h) a solvent where R<1 >and R<2 >are each independently C1-C12 fluoroalkyl groups or together R<1 >and R<2 >are joined with the N to form a (F2C)yN ring where y=4-12; R<3>, R<4>, and R<5 >are each independently selected from unsubstituted aryl, alkyl or alpha-ketomethyl groups and such groups substituted with an acid sensitive group, or R<3 >and R<4 >together with the S atom form a cycloalkylsulfonium ring; R<6 >to R<11 >and R<6'> to-R<11'> are each independently selected from branched or linear alkyl, alkoxy, halogen, hydrogen, OCO2G, OCH2CO2G, or OG where G=an acid sensitive group; where each R<12 >is independently selected from a linear, cyclic, or branched C1-C8 fluoroalkyl group, substituted or unsubstituted phenyl group, substituted or unsubstituted naphthalene group, C6-C12 cyclic or alicyclic hydrocarbon, or a linear, cyclic, or branched C1-C8 alkyl group; wherein R<13 >is selected from H, C1-C4 lower alkyl, CN, or CH2CO2R<20>; R<14 >and R<15 >are each independently selected from H, linear or branched C1-C4 alkyl, or halogen; R<16 >is H, or branched or linear C1-C4 alkyl; R<17 >is selected from substituted or unsubstituted phenyl, a substituted or unsubstituted linear, branched or cyclic C1-C20 alkyl, optionally containing an ether or ester group, a substituted or unsubstituted phenylalkylene or a substituted or unsubstituted C6< / subsc

Description

[0001] This application claims priority from U.S. Provisional Application No. 60 / 391,850, filed Jun. 26, 2002.[0002] This invention relates to photosensitive compositions with high resolution, excellent photospeed and excellent depth of focus while at the same time providing for decreasing line width and film thickness useful in the manufacture of semiconductor devices, and to the process of using such photosensitive compositions for producing imaged patterns on substrates for the production of such semiconductor devices.BACKGROUND TO THE INVENTION[0003] Advanced resists usually employ a technique called chemical amplification in which an acid generated by photolysis catalyzes a solubility switch from alkali insoluble to alkali soluble by removal of an acid sensitive group protecting an alkali solubilizing moiety. Polymers frequently used in this type of photosensitive composition include acetals derived from reaction of vinyl ethers with a polymer containing hydroxystyrene units. C...

Claims

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Application Information

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Patent Type & Authority Applications(United States)
IPC IPC(8): G03F7/004G03F7/038G03F7/039G03F7/38G03F7/40H01L21/027
CPCG03F7/0045G03F7/0046G03F7/40G03F7/0397G03F7/0392G03F7/038
Inventor BRZOZOWY, DAVIDTHOMAS, KOCAB J.HATFIELD, JOHN P.FERREIRA, LAWRENCEBLAKENEY, ANDREW
Owner FUJIFILM ELECTRONICS MATERIALS US